Trifluoroacetic acid → 2-Amino-1-(5-phenyl-[1,2,4]oxadiazol-3-yl)-butan-1-ol

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Reaction Steps

A solution of (3) (1.5 g, 4.3 mmol) in diglyme was heated at 150° C. in a microwave (Smith Creator, S00219) for 40 minutes. Solvent evaporated under vacuum in Genevac Evaporator at 80° C. for 3 hours to give a brown solid. This was taken in dichloromethyl (40 ml) and treated with trifluoroacetic acid at room temperature for 2 hours. Solvent evaporated to dryness under reduced pressure, crude taken in water, washed with DCM, aqueous layer basified with 1M NaOH solution and extracted with dichloromethyl. Organic layer dried over Na2SO4 to give pale brown solid (300 mg); 1HNMR (CDCl3) 8.14–8.10 (m, 2H), 7.59–7.47 (m, 3H), 4.83 & 4.65 (d, J=5 Hz, 1H), 3.18–3.05 (2m, 1H), 1.71–1.20(m, 2H), 1.05–0.97 (dt, J=7.2 Hz, 3H).

Provenance & Evidence